A new series of mesogenic pyran derivatives

4-[4-(3,6-Dihydro-4-methyl-2H-pyran-3-ylhydroxy)phenylaminocarbonylmethoxy]benzylidene-4-alkoxyanilines, which have the properties of smectic and nematic liquid crystals, were synthesized.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1628–1630, December, 1993.     

Liquid-crystal 4H-3,1-benzoxazln-4-ones

2,6-Disubstituted 4H-3,1-benzoxazin-4-ones that have mesogenic properties were synthesized by the reaction of 5-substituted anthranilic acid with aroyl chlorides in pyridine. The introduction of a 4H-3,1-benzoxazin-4-one fragment increases the absolute value of the anisotropy of the dielectric permeability. The temperatures and heats of the phase transitions are presented.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1335–1337, October, 1981.     

2-Aryl-4H-3,1-benzoxazin-4-ones alcoholysis

The reaction of 2-(2-tosylaminophenyl)-4H-3,1-benzoxazine-4-one with alcohols in pyridine gives tosylanthraniloylanthranilic acid esters. The synthesized compounds luminesce in the crystalline state and in solutions at room temperature. The anomalously high Stokesian shift characteristic for this series of compounds is due to intramolecular hydrogen bonding with the participation of the tosylamino group. Interaction of polar solvents and irradiation with UV light lead to cleavage of the hydrogen bond, and as a consequence, to a decrease in the Stokesian shift.     

Antimicrobial Activity of Dihydroisocoumarin Isolated from Wadi Lajab Sediment-Derived Fungus Penicillium chrysogenum: In Vitro and In Silico Study

Antibiotic resistance is considered a major health concern globally. It is a fact that the clinical need for new antibiotics was not achieved until now. One of the most commonly prescribed classes of antibiotics is β-Lactam antibiotics. However, most bacteria have developed resistance against β-Lactams by producing enzymes β-Lactamase or penicillinase. The discovery of new β-Lactamase inhibitors as new antibiotics or antibiotic adjuvants is essential to avoid future catastrophic pandemics. In this study, five dihydroisocoumarin: 6-methoxy mellein (1); 5,6-dihydroxymellein (2); 6-hydroxymellein (3); 4-chloro-6-hydroxymellein (4) and 4-chloro-5,6-di-hydroxymellein (5) were isolated from Wadi Lajab sediment-derived fungus Penicillium chrysogenum, located 15 km northwest of Jazan, KSA. The elucidation of the chemical structures of the isolated compounds was performed by analysis of their NMR, MS. Compounds 1–5 were tested for antibacterial activities against Gram-positive and Gram-negative bacteria. All of the compounds exhibited selective antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus licheniformis except compound 3. The chloro-dihydroisocoumarin derivative, compound 4, showed potential antimicrobial activities against all of the tested strains with the MIC value between 0.8–5.3 μg/mL followed by compound 5, which exhibited a moderate inhibitory effect. Molecular docking data showed good affinity with the isolated compounds to β-Lactamase enzymes of bacteria; NDM-1, CTX-M, OXA-48. This work provides an effective strategy for compounds to inhibit bacterial growth or overcome bacterial resistance.     

Reaction of Trialkyl Phosphites with Monoacylals of Dichloro- and Trichloroacetic Acids

Russian Journal of General Chemistry -     

Synthesis of polyfluorinated 4-phenyl-3,4-dihydroquinolin-2-ones and quinolin-2-ones via superacidic activation of N-(polyfluorophenyl)cinnamamides

The cyclization reactions of a series of polyfluorocinnamanilides in triflic acid (CF₃SO₃H) yield 4-phenyl-3,4-dihydroquinolin-2-ones, which include a polyfluorinated benzene moiety as a part of the quinoline scaffold. These compounds undergo dehydrophenylation in the presence of AlCl₃ to give the corresponding polyfluoroquinolin-2-ones which are converted into polyfluorinated 2-chloroquinolines on treatment with POCl₃. A mechanism for the cyclization reaction presuming the intermediacy of a superelectrophilic O,C-diprotonated form of the starting material is suggested.     

Self-Associating Systems of Alkylated 1,4-Diazabicyclo[2.2.2]octanes with Ag(I) and Gd(III) Complexes for Increasing the Solubility of Griseofulvin and Orange OT

Russian Journal of General Chemistry - Novel metallomicellar systems have been created on the basis of amphiphilic metallocomplexes of 1-hexadecyl-4-aza-1-azoniabicyclo[2.2.2]octane nitrate...     

2-Aryl-4H-3,1-benzoxazin-4-ones. Reduction

The reduction of 2-(2-tosylaminophenyl-4H-3,1-benzoxazin-4-one with zinc dust in acetic acid gives N-(o-tosylaminobenzyl)anthranilic acid, the structure of which was proved by mass spectrometry and the ¹³C NMR spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1619–1621, December, 1977.     

Reactions of Trialkyl Phosphites with Mono- and Diacylals of Halo-Substituted Acetic Acids

Trialkyl phosphites react with diacylals of di- and trichloroacetic acids by the pathway of the Perkow reaction; with monoacylals of bromo- and iodoacetic acids, by the pathway of the classical Arbuzov reaction; and with monoacylals of di- and trichloroacetic acids, by the pathway of the nonclassical Arbuzov reaction.